Two-Week Italy Self-Drive Road Trip With Itinerary from Milan to Como, Verona, Venice, Florence, Siena, and Rome

Day 2 offers a multitude of experiences. You will stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

A visit to Navigli in Milan is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Brace yourself for today’s incredible lineup of attractions in Milan, featuring fun adventures, romantic experiences, and scenic views. Start at Duomo Di Milano Museum, a world-famous church in the city. Then, head to Galleria Vittorio Emanuele Ii and soak in the ambiance of this visually striking shopping mall.

There are many interesting places to see in Milan and when you are ready for more, go to Sforzesco Castle Art Library. This is one of the city’s most impressive spots. After exploring the castle, visit the astonishing Parco Sempione. Before wrapping up your self-guided sightseeing tour, head to the locally renowned Piazza Gae Aulenti, a locally renowned public square in the city.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As dinnertime approaches, it's time to head out for a bite to eat in Milan. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Dessert Bar Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Radisson Blu Hotel Milan? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Qui Si Mangia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

After savoring a delicious meal, step into the vibrant nightlife at Kilburn Cocktail Bar Milano, where the evening is just getting started. In the same way, Bar Frida offers a unique charm perfect for experiencing the local bar scene in Milan. The Friends Pub Milano is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 4 vibrant destinations - Como, Rogaro, Lenno, and Colonno. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Como. You will spend 1 night here for some well-deserved relaxation.

Prepare for a day full of fun adventures, photo-friendly spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at Basilica Di San Fedele. This curiosity-inducing church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Saint Mary Assunta Cathedral, one of the city’s best highlights.

Next, check out Villa Carlotta (lake Como), one of the most curiosity-inducing places to see in Milan. This museum is a favorite among locals and travelers alike. Then, head to Greenway Del Lago Di Como, a top-rated hiking area that adds another dimension to your day.

When you’re done exploring for the day, you’ll drive to your hotel in Como. Check in and spend some time relaxing before you head out to tour the city.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Como. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely dining experience at L’Antica Trattoria, a popular restaurant in Como. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Como at Gesumin Restaurant, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Pronobis. It’s yet another ideal choice to enhance your time in Como tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Fresco Cocktail Shop, known for its inviting atmosphere. Bar Il Cortiletto is another great option if you’re looking for a place to get the night started. Similarly, Bar Pinocchio provides a great setting to enjoy the night away.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Verona. At the end of the day, you will enjoy the comforts of a top-rated hotel in Verona, which will be your home away from home for 1 night.

Today's adventure in Como promises more breathtaking discoveries and enriching experiences! Begin at Giusti Garden. This serene botanical garden is a highlight of any visit in the city. Then, enjoy Ponte Pietra, another history-steeped attraction that never fails to captivate visitors. Next, head over to Piazza Dei Signori, one of the city’s most worthwhile attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Delle Erbe. This standout public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Castelvecchio Museum, a locally renowned museum, and take a stroll around the area.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Verona. Verona offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Indulge in a memorable dining experience at one of Verona's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a lovely meal at La Griglia, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Vecio Macello is another top choice with a popular menu. You could also check for a table at Via Fama Cafè | Verona. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Verona tonight.

Round off your dining experience by visiting Archivio, a prime location for a drink. Alternatively, explore the distinctive characteristics of La Segreteria Café, a bar catering to every mood and preference. Grande Giove Cocktail Bar likewise offers a unique atmosphere, perfect for a memorable night out.

Relax and recharge in preparation for another adventurous day in Italy!

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Venice. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 2 nights.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the often recommended Santa Maria Della Salute, a visually striking church in Verona. Next, go to Peggy Guggenheim Collection.

After visiting Santa Maria Della Salute and Peggy Guggenheim Collection, take time to explore Verona's streets and absorb its charm. Continue your sightseeing by heading to Santa Maria Gloriosa Dei Frari. This picture-perfect church offers a unique experience. Grand Canal is another noteworthy stop.

At the end of the day, you will drive to Venice, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Venice. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Bauer Hotel, an iconic dining spot in Venice. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of L'Osteria Le Guglie, a popular restaurant in Venice. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Corner Pub, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue the enjoyment post-dinner at Al Parlamento, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, The Caffe Rosso offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Adagio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

Day 6 of your road trip across Italy promises a magnificent time exploring Venice. You have 1 night left in Venice. Take the opportunity to experience more of the best attractions and activities in the city.

Get ready to discover some of the most iconic wonders in Venice, including a historical landmark, an opera house, a public square, a church, a palace, a monument and much more! Start your day at Rialto Bridge. This history-steeped historical landmark is a wondrous place to see in Venice. Then, wander over to Teatro La Fenice. If historic sites excite you, this opera house will be right up your alley. Nearby, you’ll also find Piazza San Marco. This visually striking public square is a favorite among visitors.

Venice offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, St Mark's Basilica is a popular spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the history-steeped Doge's Palace. Take a moment to appreciate the fascinating details of this notable palace in Venice.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Indulge in a memorable dining experience at one of Venice's most popular restaurants, and connect with friendly locals for an authentic adventure.

Have a fantastic dining experience at Generator Venice, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Nevodi offers an enticing alternative with its varied menu. Additionally, Ristorante La Piazza is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Venice.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Il Mercante, known for its inviting atmosphere. The Irish Pub Venezia is another great option if you’re looking for a place to get the night started. Similarly, Ai Stagneri provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 3 nights.

Brace yourself for today’s incredible lineup of attractions in Venice, featuring family-friendly attractions, romantic experiences, and breathtaking views. Start at Piazzale Michelangelo, an astonishing observation deck in the city. Then, head to Basilica Of Santa Croce In Florence and soak in the ambiance of this heritage-rich church.

There are many interesting places to see in Venice and when you are ready for more, go to David. This is one of the city’s most popular spots. After exploring the statue, visit the well-known Central Market. Before wrapping up your self-guided sightseeing tour, head to the astonishing Cathedral Of Santa Maria Del Fiore, an astonishing church in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

On day 8 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 2 nights and discover all the best things to see and do in the area.

Don’t miss Oltrarno in Florence today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Savor the day by visiting some of the best places to see in Florence, including a historical landmark, a public square, a museum, a palace, an art gallery and much more! Start your adventure at Ponte Vecchio. This iconic historical landmark is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Della Signoria located in Florence for an enchanting atmosphere.

Next, immerse yourself in the setting of Bargello National Museum. Its detailed features will captivate you. After the museum, continue your tour of the city with a visit to Palazzo Vecchio. This palace has a history-steeped appeal. For a change of pace, head to Uffizi Gallery. As one of the most top-rated attractions in Florence, this art gallery is an excellent place to end your self-guided tour.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass and celebrate another amazing day of your road trip in Italy!

On day 9 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Pisa. You still have 1 night left in Florence.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Santa Maria Della Spina is the first of them. Spend some time admiring this symbolic church before continuing your journey. Knights' Square is your next stop. This worthwhile public square is one of the best-rated sights in Florence.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Leaning Tower Of Pisa. This historic monument is a sight to behold. To round off your sightseeing experience, visit Pisa Cathedral and Piazza Del Duomo, Pisa. If time allows, end your day with Campo Santo, a picture-perfect cemetery that offers a memorable conclusion to your exploration.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

On day 10 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Siena. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Florence is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and photo-friendly spots! Start at Porta Romana, a locally appreciated monument that is worthwhile a visit in the city. Nearby, you’ll find Palazzo Salimbeni, enchanting visitors with its culturally significant appeal. Continue your exploration at Basilica Of San Domenico. This church is one of the city’s most increasingly popular spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Siena Cathedral. After exploring the church, head to the increasingly popular Pubblico Palace. This palace will wrap up today’s self-guided sightseeing tour in the city.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Siena. Siena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Experience an unparalleled adventure on day 11 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 3 nights here for some well-deserved relaxation.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Colosseum. This wondrous archeological site is a culturally significant place to see in Siena. Continue your discovery at Roman Forum, an UNESCO world heritage-listed archeological site with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Del Popolo. This impressive public square offers a masterful encounter with Siena. Next, make your way to Capitoline Museums to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

At the end of the day, you will drive to Rome, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Treat yourself to a delightful dinner at La Bottega Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Pasta In Corso? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Vecchia Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

Get a good night's sleep and look forward to another great day on the road in Italy!

Wake up to day 12 of your extraordinary road trip in Italy. With 2 nights left in Rome, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Trastevere is a neighborhood that stands out as one of the must-see places in Vatican City. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

A blend of family-friendly attractions, romantic experiences, and photo-friendly spots await you in Rome on today’s itinerary. First up is the globally renowned art museum, Vatican Museums. Afterward, continue to Sistine Chapel, a chapel every traveler should visit.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to St. Peter's Basilica. This timeless major basilica is an essential stop. Following that, head to Campo De' Fiori, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Navona, a globally renowned public square in the city.

When you’re done exploring for the day, you’ll return to Rome and your accommodation.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Enjoy a delicious meal at RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Round off your dining experience by visiting Sant' Eustachio Caffè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yellowsquare Rome, a bar catering to every mood and preference. Caffè Portofino likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

Day 13 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Basilica Of San Clemente. This frequently visited church provides an insightful glimpse into the city's identity. Next, discover Spanish Steps, a romantic public square, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Di Spagna, an iconic public square. When you’re done, don’t forget to make a stop at the wondrous Trevi Fountain. Round off your day at Pantheon, another gem in Rome with inviting features to discover.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

Savor the flavors at Hotel de Russie, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider The Parrot Bar. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

Say good night to Rome and look forward to another great day of your road trip in Italy!

Embark on another extraordinary experience on day 14 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Bologna Cathedral. This locally appreciated church provides an insightful glimpse into the city's identity. Next, discover Piazza Maggiore, a grand public square, promising a delightful encounter.

Continue your sightseeing with a visit to Two Towers, a popular monument. When you’re done, don’t forget to make a stop at the underrated Porta Maggiore.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and spend some time relaxing before you head out to tour the city.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Milan. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Bice Restaurant, a highly-rated dining destination in Milan. If you're eager to try something different, consider Alto Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bhangrabar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Rufus Cocktail Bar offers an ideal atmosphere to enjoy the pleasures of the night. Ostello Bello Grande is also a great option that provides a perfect setting for a relaxing evening.

Take some time to reflect on your day and savor another beautiful night in Italy.